2-Bromoethanol → (S)-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1604035Notes

Reaction equation

HRID 1604035 reaction equation
[CH3:1][C@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:11][CH2:12]O>ClCCl>[CH3:1][C@H:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:12][CH2:11][NH:9]1

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 758181-Phenethylamine, (-)-

Product 1

HCID 11205845(S)-1-methyl-1,2,3,4-tetrahydroisoquinolineYield 88,312.602%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
51 °C

Procedure

108.23 g(0.903 mmole) of (S)-(-)-α-methylbenzylamine was dissolved in 140 ml of dichloromethane and 144.0 g(1.071 mmole) of 2-bromoethanol was added thereto. This mixture was stirred at 51° C. for 52 hours to complete the reaction. The reaction solution was concentrated under reduced pressure and the residue was subjected to fractional distillation to obtain 117.4 g of the title compound, which had a pale yellow color.

Workup

  1. customthe reaction
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. distillationthe residue was subjected to fractional distillation

Sources & evidence

ORD record
ord-2849bda1334a4a04b0a508704538893d
Source dataset
uspto-grants-1999_11
Patent number
US05990311

Reaction notes

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